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Well..considering we don't know what you know, its going to be very difficult to figure out what you need to ask. The best way to build questions is take what you know, and figure out what you are really interested in

If he played football/baseball/cricket/rugby - what team, where, why,what position
If he likes to read - what kind of books, how often
If he likes to game - board, rpg, everything. Is he a GM/DM, what kind of gaming sessions does he like, his longest, his shortest

etc..etc..etc...

I don't really have any suggestions beyond taking what you know, finding something thats interests YOU about HIM and asking questions about it.

for example..here are the base questions she came up with. Some interesting ones in there actually

Quote:

What's your favorite hiking path in Portland?
If you could make one law that everyone had to follow, what would it be?
What is your favorite memory from high school?
What's your worst memory from grade school?
If you could go anywhere in the world for a month, allexpenses paid, where would you go? (Take note, and perhaps you can tailor your next trip to include some of those elements in it.)
What's your idea of the worst job you can ever imagine?
What's your favorite comfort food? (Take note, then when they have a bad day, you can make/get it for them, and they will feel really good that you remembered and care about them.)
What's worse for you, getting too little sleep or not being able to work out?
What do you think your life would be like if you were famous?
Who are your favorite authors?
What's your definition of hell?
If you were going to get a pet, what would you get, where would you get it and what would you name it? (Okay, that is three questions; beware not to make your questions too long or too involved.)
What's your idea of the perfect day?
Would you ever run for elected office?
Who's your favorite local band?
If you couldn't live in the Portland area, where would you live?
What's the craziest living situation you've ever experienced?
If you were given $1000, what would you do with it?
If you were given $100,000,000, what would you do with it?
Who do you admire the most?

Hope this doesn't end up being a one sided conversation specialist. Those are some very difficult people to talk to